SU1480770A3 - Способ получени пирроло-бензимидазолов или их физиологически совместимых солей с неорганическими кислотами - Google Patents
Способ получени пирроло-бензимидазолов или их физиологически совместимых солей с неорганическими кислотами Download PDFInfo
- Publication number
- SU1480770A3 SU1480770A3 SU853894709A SU3894709A SU1480770A3 SU 1480770 A3 SU1480770 A3 SU 1480770A3 SU 853894709 A SU853894709 A SU 853894709A SU 3894709 A SU3894709 A SU 3894709A SU 1480770 A3 SU1480770 A3 SU 1480770A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dihydro
- pyrrolo
- pyridyl
- group
- dimethyl
- Prior art date
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- 150000007522 mineralic acids Chemical class 0.000 title claims abstract 5
- 150000003839 salts Chemical class 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 title claims description 5
- BKOVMXWXILSWCU-UHFFFAOYSA-N pyrrolo[3,2-e]benzimidazole Chemical class C1=CC2=NC=CC2=C2N=CN=C21 BKOVMXWXILSWCU-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- 229910052717 sulfur Chemical group 0.000 claims abstract 4
- 239000011593 sulfur Chemical group 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000001118 alkylidene group Chemical group 0.000 claims abstract 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 3
- 230000002378 acidificating effect Effects 0.000 claims abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000008064 anhydrides Chemical class 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004185 ester group Chemical group 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 94
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 37
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 235000019439 ethyl acetate Nutrition 0.000 claims description 13
- -1 chlorate nicotinic acid - hydrochloride Chemical compound 0.000 claims description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- WOXQTRUXNFNMDU-UHFFFAOYSA-N benzimidazol-5-one Chemical compound O=C1C=CC2=NC=NC2=C1 WOXQTRUXNFNMDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- HHDYSDWIZLXLDU-UHFFFAOYSA-N 5,6-diamino-3,3-dimethyl-1h-indol-2-one Chemical compound NC1=C(N)C=C2C(C)(C)C(=O)NC2=C1 HHDYSDWIZLXLDU-UHFFFAOYSA-N 0.000 claims 6
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- NPRZWOJTSGFSBF-UHFFFAOYSA-N 2-chloropyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC(Cl)=C1 NPRZWOJTSGFSBF-UHFFFAOYSA-N 0.000 claims 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims 1
- LNYYVHNIHCOWCB-UHFFFAOYSA-N 2-methylpyridine-4-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC=N1 LNYYVHNIHCOWCB-UHFFFAOYSA-N 0.000 claims 1
- AIWBTDBUNGZIQG-UHFFFAOYSA-N 2-oxo-1h-pyridine-4-carbonyl chloride Chemical compound ClC(=O)C=1C=CNC(=O)C=1 AIWBTDBUNGZIQG-UHFFFAOYSA-N 0.000 claims 1
- AASOBSCZLSEAQQ-UHFFFAOYSA-N 6-methylpyridine-3-carbonyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=N1 AASOBSCZLSEAQQ-UHFFFAOYSA-N 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- ZFCTXAHHPGHXPS-UHFFFAOYSA-N C=C(C(O)=O)C1=CC=CN=C1.Cl Chemical compound C=C(C(O)=O)C1=CC=CN=C1.Cl ZFCTXAHHPGHXPS-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- UQRTVNHZSVCGMI-UHFFFAOYSA-N benzimidazole-5-thione Chemical compound S=C1C=CC2=NC=NC2=C1 UQRTVNHZSVCGMI-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000006378 chloropyridyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- GFOGPMFLGWHHJF-UHFFFAOYSA-N indazol-6-one Chemical compound O=C1C=CC2=CN=NC2=C1 GFOGPMFLGWHHJF-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000021178 picnic Nutrition 0.000 claims 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 230000004071 biological effect Effects 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- VVEJNQMYFCSJIN-UHFFFAOYSA-N 5,6-diamino-1,3-dihydroindol-2-one Chemical compound C1=C(N)C(N)=CC2=C1NC(=O)C2 VVEJNQMYFCSJIN-UHFFFAOYSA-N 0.000 abstract 1
- 229910020514 Co—Y Inorganic materials 0.000 abstract 1
- 235000009499 Vanilla fragrans Nutrition 0.000 abstract 1
- 244000263375 Vanilla tahitensis Species 0.000 abstract 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- WSPRZQBQPDVXOA-UHFFFAOYSA-N 5-amino-3,3-dimethyl-6-nitro-1h-indol-2-one Chemical compound [O-][N+](=O)C1=C(N)C=C2C(C)(C)C(=O)NC2=C1 WSPRZQBQPDVXOA-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- UMHSOWVJQJFESZ-UHFFFAOYSA-N 3,3-dimethyl-5-nitro-1h-indol-2-one Chemical compound C1=C([N+]([O-])=O)C=C2C(C)(C)C(=O)NC2=C1 UMHSOWVJQJFESZ-UHFFFAOYSA-N 0.000 description 2
- JTVMMOAEEVKAGQ-UHFFFAOYSA-N 3,3-dimethyl-6-nitro-1h-indol-2-one Chemical compound [O-][N+](=O)C1=CC=C2C(C)(C)C(=O)NC2=C1 JTVMMOAEEVKAGQ-UHFFFAOYSA-N 0.000 description 2
- IWARVYFPBLDOAK-UHFFFAOYSA-N 6-amino-3,3-dimethyl-1h-indol-2-one Chemical compound NC1=CC=C2C(C)(C)C(=O)NC2=C1 IWARVYFPBLDOAK-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- XNKHQYMRJZDJSE-UHFFFAOYSA-N n-(3,3-diethyl-6-nitro-2-oxo-1h-indol-5-yl)acetamide Chemical compound [O-][N+](=O)C1=C(NC(C)=O)C=C2C(CC)(CC)C(=O)NC2=C1 XNKHQYMRJZDJSE-UHFFFAOYSA-N 0.000 description 2
- WANVWWNIVMVTTM-UHFFFAOYSA-N n-(3,3-dimethyl-2-oxo-1h-indol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2NC(=O)C(C)(C)C2=C1 WANVWWNIVMVTTM-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- JOAHCWIICCHHOU-UHFFFAOYSA-N 3,3-diethyl-1h-indol-2-one Chemical compound C1=CC=C2C(CC)(CC)C(=O)NC2=C1 JOAHCWIICCHHOU-UHFFFAOYSA-N 0.000 description 1
- KEZHRKOVLKUYCQ-UHFFFAOYSA-N 3,3-dimethyl-1h-indol-2-one Chemical compound C1=CC=C2C(C)(C)C(=O)NC2=C1 KEZHRKOVLKUYCQ-UHFFFAOYSA-N 0.000 description 1
- JEHGATQUCUYHJL-UHFFFAOYSA-N 3-hydroxypyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1O JEHGATQUCUYHJL-UHFFFAOYSA-N 0.000 description 1
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- SUKYJAWZLKJMOR-UHFFFAOYSA-N pyridine-4-carbonyl chloride;dihydrochloride Chemical compound Cl.Cl.ClC(=O)C1=CC=NC=C1 SUKYJAWZLKJMOR-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843417643 DE3417643A1 (de) | 1984-05-12 | 1984-05-12 | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
| DE19843446417 DE3446417A1 (de) | 1984-12-20 | 1984-12-20 | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1480770A3 true SU1480770A3 (ru) | 1989-05-15 |
Family
ID=25821132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853894709A SU1480770A3 (ru) | 1984-05-12 | 1985-05-10 | Способ получени пирроло-бензимидазолов или их физиологически совместимых солей с неорганическими кислотами |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2443704C1 (ru) * | 2010-10-29 | 2012-02-27 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" | СУЛЬФАТЫ 2-АРИЛ-4-ДИАЛКИЛАМИНОЭТИЛ-3-ФЕНИЛПИРРОЛО[1,2-a]-БЕНЗИМИДАЗОЛОВ, ОБЛАДАЮЩИЕ АНТИОКСИДАНТНЫМИ И АНТИРАДИКАЛЬНЫМИ СВОЙСТВАМИ |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL147842B1 (en) * | 1984-05-12 | 1989-08-31 | Method of obtaining novel pyroisobenzimidazoles | |
| DE3445669A1 (de) * | 1984-12-14 | 1986-06-19 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3501497A1 (de) * | 1985-01-18 | 1986-07-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
| DE3524067A1 (de) * | 1985-07-05 | 1987-01-08 | Boehringer Mannheim Gmbh | Neue benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
| DE3530825A1 (de) * | 1985-08-29 | 1987-03-05 | Boehringer Mannheim Gmbh | Neue benzodipyrrole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3531678A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3626664A1 (de) * | 1986-08-07 | 1988-02-11 | Boehringer Mannheim Gmbh | Tricyclische benzotriazole, verfahren zu ihrer herstellung sowie arzneimittel |
| DE3639466A1 (de) * | 1986-11-18 | 1988-05-19 | Thomae Gmbh Dr K | Neue pyrrolo-benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3642315A1 (de) * | 1986-12-11 | 1988-06-23 | Boehringer Mannheim Gmbh | Neue pyrrolobenzimidazole, verfahren zu ihrer herstellung sowie arzneimittel |
| DE3740985A1 (de) * | 1987-12-03 | 1989-06-15 | Boehringer Mannheim Gmbh | Verwendung linear anellierter tricyclen als hemmer der erythrozytenaggregation |
| US4963677A (en) * | 1987-12-30 | 1990-10-16 | Orion Corporation Ltd. | Heterocyclic lactam compounds |
| ATE138658T1 (de) * | 1987-12-30 | 1996-06-15 | Orion Yhtymae Oy | Heterocyclische verbindungen |
| DE3803775A1 (de) * | 1988-02-09 | 1989-08-17 | Boehringer Mannheim Gmbh | Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| US5324911A (en) * | 1990-01-08 | 1994-06-28 | Schroer Manufacturing Company | Heated animal surgery table |
| DE4027592A1 (de) * | 1990-08-31 | 1992-03-05 | Beiersdorf Ag | Neue pyrrolobenzimidazole, imidazobenzoxazinone und imidazochinolone, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US20060142247A1 (en) * | 2004-12-17 | 2006-06-29 | Guy Georges | Tricyclic heterocycles |
| EP1879894A1 (en) * | 2005-04-14 | 2008-01-23 | F.Hoffmann-La Roche Ag | Aminopyrazole derivatives, their manufacture and use as pharmaceutical agents |
| ATE409190T1 (de) * | 2005-04-14 | 2008-10-15 | Hoffmann La Roche | Tricyclische azolderivate, ihre herstellung und ihre verwendung als pharmazeutische mittel |
| EP1966213A1 (en) * | 2005-12-15 | 2008-09-10 | F.Hoffmann-La Roche Ag | Tricyclic lactam derivatives, their manufacture and use as pharmaceutical agents |
| US20090291968A1 (en) * | 2006-03-23 | 2009-11-26 | Guy Georges | Substituted indazole derivatives, their manufacture and use as pharmaceutical agents |
| US8063225B2 (en) | 2006-08-14 | 2011-11-22 | Chembridge Corporation | Tricyclic compound derivatives useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders |
| EA020466B1 (ru) | 2007-06-04 | 2014-11-28 | Синерджи Фармасьютикалз Инк. | Агонисты гуанилатциклазы, пригодные для лечения желудочно-кишечных нарушений, воспаления, рака и других заболеваний |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EP2810951B1 (en) | 2008-06-04 | 2017-03-15 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| JP2011528375A (ja) | 2008-07-16 | 2011-11-17 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CA3100941C (en) | 2011-03-01 | 2024-03-05 | Synergy Pharmaceuticals Inc. | Process of preparing guanylate cyclase c agonists |
| BR112015005186A2 (pt) | 2012-09-13 | 2017-07-04 | Hoffmann La Roche | 2-oxo-2,3-di-hidro-indóis para tratamento de distúrbios do snc |
| EP3718557A3 (en) | 2013-02-25 | 2020-10-21 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonist sp-333 for use in colonic cleansing |
| WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼｃの超高純度アゴニスト、その作成および使用方法 |
| CN114404588A (zh) | 2013-08-09 | 2022-04-29 | 阿德利克斯公司 | 用于抑制磷酸盐转运的化合物和方法 |
| GB201709456D0 (en) * | 2017-06-14 | 2017-07-26 | Ucb Biopharma Sprl | Therapeutic agents |
| CN114340631A (zh) | 2019-05-21 | 2022-04-12 | 阿德利克斯股份有限公司 | 用于降低患者的血清磷酸盐的组合 |
| JP6854953B1 (ja) | 2020-06-16 | 2021-04-07 | 株式会社ソディック | ワイヤ放電加工装置 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1158532A (en) * | 1967-01-05 | 1969-07-16 | Centre Nat Rech Scient | 2-Oxoindoline-3-Carboxylic Acids and Esters thereof |
| BE714717A (enrdf_load_stackoverflow) * | 1967-05-12 | 1968-09-30 | ||
| FR1529901A (fr) * | 1967-05-12 | 1968-06-21 | Centre Nat Rech Scient | Procédé de préparation de lactames se rattachant à l'indolinone et à l'oxo quinoléine |
| US4322533A (en) * | 1980-03-17 | 1982-03-30 | Lesher George Y | 1H-Indole-2,3-dione derivatives |
| CH644116A5 (de) * | 1980-08-21 | 1984-07-13 | Hoffmann La Roche | Imidazolderivate. |
| DE3224512A1 (de) * | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| PL147842B1 (en) * | 1984-05-12 | 1989-08-31 | Method of obtaining novel pyroisobenzimidazoles |
-
1985
- 1985-05-06 PL PL1985259261A patent/PL147842B1/pl unknown
- 1985-05-06 PL PL1985253246A patent/PL144822B1/pl unknown
- 1985-05-06 GR GR851085A patent/GR851085B/el unknown
- 1985-05-07 NZ NZ212005A patent/NZ212005A/xx unknown
- 1985-05-07 IL IL75120A patent/IL75120A/xx unknown
- 1985-05-07 US US06/731,500 patent/US4666923A/en not_active Expired - Lifetime
- 1985-05-08 PH PH32240A patent/PH22863A/en unknown
- 1985-05-09 ES ES542976A patent/ES542976A0/es active Granted
- 1985-05-09 AU AU42222/85A patent/AU560349B2/en not_active Ceased
- 1985-05-09 EP EP85105675A patent/EP0161632B1/de not_active Expired - Lifetime
- 1985-05-09 PT PT80425A patent/PT80425B/pt not_active IP Right Cessation
- 1985-05-09 DE DE8585105675T patent/DE3582447D1/de not_active Expired - Lifetime
- 1985-05-09 KR KR1019850003144A patent/KR870001201B1/ko not_active Expired
- 1985-05-10 FI FI851869A patent/FI81351C/fi not_active Application Discontinuation
- 1985-05-10 HU HU851775A patent/HU193754B/hu not_active IP Right Cessation
- 1985-05-10 SU SU853894709A patent/SU1480770A3/ru active
- 1985-05-10 NO NO851862A patent/NO851862L/no unknown
- 1985-05-10 DK DK209585A patent/DK209585A/da not_active Application Discontinuation
- 1985-05-13 JP JP60099742A patent/JPH0647593B2/ja not_active Expired - Lifetime
-
1988
- 1988-07-05 US US07/217,143 patent/US4963686A/en not_active Expired - Fee Related
-
1993
- 1993-12-10 JP JP5310823A patent/JPH0772185B2/ja not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Эльдерфилд Р. Гетероциклические соединени . Т. V. М.: Изд-во ИЛ, 1954, с. 217. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2443704C1 (ru) * | 2010-10-29 | 2012-02-27 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" | СУЛЬФАТЫ 2-АРИЛ-4-ДИАЛКИЛАМИНОЭТИЛ-3-ФЕНИЛПИРРОЛО[1,2-a]-БЕНЗИМИДАЗОЛОВ, ОБЛАДАЮЩИЕ АНТИОКСИДАНТНЫМИ И АНТИРАДИКАЛЬНЫМИ СВОЙСТВАМИ |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0161632A3 (en) | 1986-06-11 |
| IL75120A (en) | 1989-02-28 |
| GR851085B (enrdf_load_stackoverflow) | 1985-11-25 |
| IL75120A0 (en) | 1985-09-29 |
| PT80425B (de) | 1987-04-16 |
| PL147842B1 (en) | 1989-08-31 |
| JPH0741474A (ja) | 1995-02-10 |
| JPH0647593B2 (ja) | 1994-06-22 |
| FI851869A0 (fi) | 1985-05-10 |
| ES8603178A1 (es) | 1986-01-01 |
| US4963686A (en) | 1990-10-16 |
| HU193754B (en) | 1987-11-30 |
| US4666923A (en) | 1987-05-19 |
| KR850008170A (ko) | 1985-12-13 |
| PL144822B1 (en) | 1988-07-30 |
| JPS60246386A (ja) | 1985-12-06 |
| DE3582447D1 (de) | 1991-05-16 |
| AU4222285A (en) | 1985-11-14 |
| DK209585A (da) | 1985-11-13 |
| PT80425A (de) | 1985-06-01 |
| FI81351B (fi) | 1990-06-29 |
| HUT37938A (en) | 1986-03-28 |
| ES542976A0 (es) | 1986-01-01 |
| DK209585D0 (da) | 1985-05-10 |
| AU560349B2 (en) | 1987-04-02 |
| JPH0772185B2 (ja) | 1995-08-02 |
| PH22863A (en) | 1989-01-19 |
| FI851869L (fi) | 1985-11-13 |
| PL253246A1 (en) | 1986-08-26 |
| NZ212005A (en) | 1989-07-27 |
| KR870001201B1 (ko) | 1987-06-20 |
| NO851862L (no) | 1985-11-13 |
| EP0161632A2 (de) | 1985-11-21 |
| EP0161632B1 (de) | 1991-04-10 |
| FI81351C (fi) | 1990-10-10 |
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